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Chemical Structure| 187273-03-6 Chemical Structure| 187273-03-6

Structure of 187273-03-6

Chemical Structure| 187273-03-6

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Product Details of [ 187273-03-6 ]

CAS No. :187273-03-6
Formula : C9H6ClNO2
M.W : 195.60
SMILES Code : N#CC1=CC(Cl)=CC(C(C)=O)=C1O
MDL No. :MFCD13178302

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Application In Synthesis of [ 187273-03-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 187273-03-6 ]

[ 187273-03-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 13589-72-5 ]
  • [ 187273-03-6 ]
  • 2
  • [ 13589-72-5 ]
  • [ 198902-28-2 ]
  • [ 187273-03-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium chloride; sulfuric acid;aluminium trichloride; In water; acetic anhydride; Further, 39.25 g (0.25 mol) of the <strong>[13589-72-5]5-chloro-2-hydroxybenzonitrile</strong> were dissolved in 40 ml of acetic anhydride, followed by the addition of 0.5 ml of concentrated sulfuric acid. After the reaction mixture was heated at 60 C. for 10 minutes, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with 1N NaOH and a saturated aqueous solution of sodium chloride and was then dried over Na2 SO4. The solvent was distilled off under reduced pressure, whereby 45 g of 2-acetoxy-5-chlorobenzonitrile (yield: 92%). A mixture of 44 g of the 2-acetoxy-5-chlorobenzonitrile and 99 g (0.75 mol) of aluminum chloride was then heated at 160 C. for 3 hours. The reaction mixture was allowed to cool down to room temperature, and was then poured into ice water which contained 100 ml of concentrated hydrochloric acid. The slurry was extracted with ethyl acetate (3*350 ml). The extract was washed with 1N hydrochloric acid (3*200 ml) and a saturated aqueous solution of sodium chloride (400 ml) and was then dried over Na2 SO4. The solvent was distilled off under reduced pressure. The residue was washed with dichloromethane to remove byproducts, and was then collected by filtration, whereby 16.5 g of the title compound were obtained as brown powder (yield: 38%). Melting point: 137.9-139.8 C. 1 H-NMR(CDCl3)delta(ppm): 2.72(3H,s,COCH3), 8.21(1H,d,J=2.5 Hz,H4/6), 8.32(1H,d,J=2.5 Hz,H4/6), 12.77(1H,brs,ArOH).
 

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• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Blaise Reaction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Thorpe-Ziegler Reaction • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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